Summary of The Season

Go short, long, or in between: Dressing in an era where (almost) anything goes.

Do you ever long for the days when fashion trends were handed down from the little-gilt-chair brigade like the Ten Commandments? Me neither. We're all grown-ups and have learned by now that even the best trends are worth following only if they work for us. In that spirit, perhaps it's time to regard them more as suggestions. Which comes as a relief, considering that this season, so many trends seem to be diametrically opposed. Short. And long. Embellished. And nun-like. Lushly feminine. And coolly masculine. With such wildly divergent options, you'd be forgiven for assuming that anything goes.

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Believe me, it doesn't. A peep-toe with a brick-like platform will date you faster than an iPhone 3 with shattered glass. A huge-shouldered jacket from three years ago looks like something … from three years ago, rather than the "timeless classic" that you hoped its four-figure price tag would deliver. A hem that's two inches above the knees? Tragic.

A word or two more about length. Once it was the number one marker of a fashionable look; now, aside from the two-inch rule, we can laugh in the face of such one-size-fits-all diktats. Lengths, I am overjoyed to report, are all over the map: shin-sweeping at Derek Lam, Céline, and Roksanda; shrunken at Saint Laurent and Louis Vuitton. Choose what's most flattering, make sure it's pleated, bias-cut, A-line, or ruffle-hemmed—anything but a tube—and

get the shoes right. (When even Victoria Beckham, she of stilettos-on-a-treadmill fame, says, "For me, it's all about a flat," you know it's time to embrace a lower-heeled brogue, skate shoe, or Chelsea boot.)

This season, coats are all over the place, stylistically and otherwise. I'm feeling for the long, fit-and-flare (waist) coats at Céline. Though calf-grazing, they are the acme of outerwear aspirations but best left to Karlie Kloss. (It's a height thing.) The opposite of the ankle sweeper is a fitted, shorter style. Saint Laurent's tweed trench and Vuitton's leather version brushed the thighs, and you just know the cool girls (Edie Campbell, Charlotte Gainsbourg) will be slouching all around town in them.

"A peep-toe with a brick-like platform will date you faster than an iPhone 3 with shattered glass." —Lisa Armstrong

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The third, equally viable option is the double-face wool-felt or cashmere wrap coat. Agnona's camel one—there are a lot of caramel colors about, by the way—looks like (and almost costs) a million bucks. Altuzarra's contrast-hued shawl-collar dressing-gown toppers are fabulous and pragmatic; adjust that belt to fit. Dries Van Noten got belt happy too, using a wide metallic band to cinch a stripy coat high on the torso. Lesson: Revisit and revive your belt armory. The optimal coat length? Just below the knee, unless it's a cape, which it may well be, once you've seen the fabulously soft, cardigan-light ones at Rick Owens and Valentino.

But maybe you're think-ing about an animal-print coat. I won't judge you. It's a classic. These days it's also a neutral—in skilled hands—most notably at Sportmax, where it was mixed with lots of can't-go-wrong black.

We shouldn't forget shearling either. Miuccia Prada has called it "poor fur … in the past it was for people who couldn't afford mink or sable." Not anymore. Prada's matte or metallic leather three-quarter-length coat jackets, lined with daffodil or crimson sheepskin, are some of the season's most memorable and provide another piece in the what-length-to-wear-with-long-skirts jigsaw.

If endless playing with proportions strikes you as time you could better spend catching up on Netflix series, then skip the skirt conundrum and move directly to pants. Just not your trusty drainpipes. The new shaped pants (as seen at Marc Jacobs, Dior, and Hermès) are looser, higher, friendlier. For one thing, they won't give you a blood clot—or a calf complex.

The latest rule of pants is to go only for those that make your legs look longer. Counterintuitively, that doesn't mean they must skim the tops of your shoes. Even if you're on the short side, pants that are cropped above the ankle, like the ones at Michael Kors and Derek Lam, can flatter if the waist sits on or above your navel and you wear them with a medium block heel, as seen at Valentino and Christopher Kane. In many ways this length offers the most flexibility. It allows for some ankle display in warmer weather, which helps keep a masculine look on the gamine side of butch. In the depths of winter it works with a shin-high, block-heeled, round-toed boot from Dries Van Noten or Marc Jacobs—probably the single most important buy in the coming months.

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In addition to your seven-eighths-length pants, you'll need something longer and drapier—maybe in black or cream silk crepe, with a satin stripe—to wear at cocktail parties. Slouchy elegance is still a key fashion aspiration, especially for evening. And if we're talking serious investment, you can do no better than to match your pants with one of Raf Simons's Dior tuxedo jackets. I've tried a few, and his are the keepers. Remind you of anything? Fashion's going a bit '70s—not in the scary, glam-rock way but rather in a Julie ChristieDon't Look Now moment. Do check Christie's outfits on YouTube—they're far more thrilling than that supposedly shocking sex scene. Less dated too.

One reason that her wardrobe still exerts such allure 40 years on is that it's exemplary of moderation and effortlessness. The 2014 version of the faintly sparkly top she slips into for a resurrection dinner with her husband would be one of Salvatore Ferragamo's cashmere sweaters and iridescent skirts in metallic bronze.

The Christie film may be angsty, but the style certainly isn't. Take your cue from it and have fun with some of 2014's tropes: a fringe tongue on a flat golfing brogue or as a trim on your bag; a zip-embellished biker jacket; the single dangly earring (à la Céline)—they're all touches that will add personality. But now doesn't feel like the time for tortured, extreme fashion. Even the bag of the season, Fendi's small By the Way style, is minimalist and—trust me—big enough for everything you need.Utterly plain, save for its sneaky alligator-tail trim, it's a paradigm of understated timelessness. That's the real signature of this season.

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